Oak McCullough

Randy and Wes welcome back a familiar favorite—Lieutenant Colonel (Retired) Oak McCullough- in this heartfelt, high-energy episode of Building Wins LIVE. Known not only for his decorated military service but also for his passionate keynote talks and leadership training, Oak brings the kind of wisdom you don’t just hear—you feel.

The episode starts with classic camaraderie, highlighting the friendships and networking that grow from shared values and mutual respect. Oak’s return to the show isn’t just a guest spot—it’s a reunion. He and Randy reflect on past meetups, plans, and the unique bond that builds when leaders connect beyond the stage.

Oak shares how his career evolved from a small-town Illinois upbringing to commissioning over 600 Army officers, deploying in Desert Storm, and delivering leadership talks nationwide. His current mission? Passing the torch. From ROTC classrooms to corporate conferences, Oak emphasizes that leadership is a privilege, not a position. Key themes include:

• Why real leaders get out from behind the desk
• The importance of knowing your people personally, not just professionally
• How assigning the right task to the right person increases both morale and results
• Why “celebrate today—it’s the last day it’s about you” still rings true for new leaders

The conversation also dives deep into Oak’s book, Your Leadership Legacy . Designed to be practical, not theoretical, the book offers chapter-by-chapter takeaways and personal reflection prompts, making it a go-to desk companion for new and seasoned leaders. Oak reveals how the book was born from a challenge at a church event and was written in less than a year. Bonus: Oak himself voices the audiobook.

Before wrapping up, Oak discusses his “Four F’s” method for recharging—faith, Family, Friends, and Fishing—and why leaders must protect their energy to lead effectively. He teases his upcoming second book, Arm Yourself for Success , and shares his excitement about reworking his website, media kit, and speaker reel.

Whether you’re a leader, aspire to be one, or love learning from real people doing impactful work, this episode is packed with wisdom, humor, and heartfelt perspective. As always, Randy and Wes bring out the best in their guests—and each other.

🛠️ Get Oak’s book on Amazon (paperback, hardback, ebook, or audio)

🎧 Follow Oak and stay tuned for the release of his next book

📍 Learn more and watch past episodes at BuildingWins.live

Until next time, go make today your best day ever (Until tomorrow)! 🙌